Stereochemically controlled syntheses of indole-substituted dihydrofuran-2-ones and a pyrrolidin-2-one

  • Boisbrun M
  • Kovács-Kulyassa Á
  • Jeannin L
 et al. 
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Abstract

In order to obtain constrained analogues of tryptophane, five-membered lactams and lactones bearing 4-indolyl and 3-carboxylic groups were prepared in a completely diastereoselective manner, resulting in a trans relationship. Furthermore, the use of chiral precursors in the synthesis yielded enantiomerically pure compounds with three contiguous chiral centres. © 2000 Elsevier Science Ltd.

Author-supplied keywords

  • Indoles
  • Lactams
  • Lactones
  • Stereocontrol

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